Southwest® flights from Kansas City to Chicago (Midway) from $80

When you think of the City of the Big Shoulders, there’s a good chance you picture the iconic skyline. When you visit Chicago, you can take in the view by land or sea (or, more accurately, lake or river) with popular tours, or you can view the skyline from within it. The Chicago Skydeck Ledge lets you step four feet out from the building, placing you 1,353 feet above the busy streets of downtown Chicago. If your nerves don’t take your breath away, the view sure will.

There’s more to see in Chicago than the skyline, of course. Museum fans are in for a treat and should consider a trip to one of the several that the city boasts. The Art Institute, the Field Museum, the Museum of Contemporary Art, the American Writers Museum, and the Museum of Science and Industry are all conveniently located near the Loop (what locals call the city’s downtown); the Chicago History Museum is further north, but should not be missed for true lovers of the town. More interested in flora and fauna than man-made masterpieces? Chicago boasts the Shedd Aquarium and Lincoln Park Zoo inside city limits, Brookfield Zoo in the western suburbs, and the Chicago Botanic Gardens in the northern suburbs. The latter two are easily accessible via Metra train.